4,211

Berkshire, MA Homes

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  • /25

    $335,000

    • 3 Beds
    • 1.5 Baths
    • 1,232 Sq Ft

    182 Church St, Canaan, CT 06018

    Welcome to this classic 3-bedroom Colonial, ideally situated on the outskirts of town yet just a short stroll to the sidewalk district. This home blends timeless charm with functional living spaces, perfect for families or anyone looking for a comfortable setting with easy access to town amenities. Step inside to discover hardwood floors that flow throughout the home, adding warmth and character

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 295-3073

    182 Church St, Canaan, CT 06018
  • /19

    $3,300 per month

    • 1 Bed
    • 1.5 Baths
    • 1,900 Sq Ft
    • House for Rent

    174 Weatogue Rd, Salisbury, CT 06068

    Enjoy a unique retreat at the Lodge! This fully furnished rental boasts a large open floor plan that includes kitchen/dining area, seating area in front of large stone fireplace, sleigh bed, tv area and a beautiful custom bar. One full bath and one half bath. Plenty of space for a gathering or just a few. Vacation at the Lodge and enjoy the beauty of the Northwest Corner of Connecticut.

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 734-4642

    174 Weatogue Rd, Salisbury, CT 06068
  • /37

    $644,000 Sold Aug 01, 2025

    • 1,224 Sq Ft
    • $526/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    284 Brewer Branch Rd, Great Barrington, MA 01230

    MID CENTURY MODERN: Built in 1973 of a minimalist design. This very cool home is tucked on a country road. Three bedrooms, two baths with upper level open plan overlooking beautiful light forest. A Fire place anchors the lovely open concept with a wall of windows letting in the sunshine. Perfect as a short term rental when not in use offering guests a beautiful in-ground pool to cool off in the

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    284 Brewer Branch Rd, Great Barrington, MA 01230
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft

      206 E Main St, Ashley Falls, MA 01222

      206 E Main St, Ashley Falls, MA 01222
  • /36

    $899,000

    • 2 Beds
    • 2.5 Baths
    • 1,508 Sq Ft

    48 Preston Ln, Salisbury, CT 06068

    Tucked away on a private road with shared lake access to the serene waters of Lake Washinee, this custom one-level home offers the perfect blend of natural beauty, thoughtful design, and modern comfort. Set on just over three wooded acres with a tranquil stream, the property offers privacy and peaceful surroundings in every direction. The original home was built in 1950. There was a complete

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 792-5920

    48 Preston Ln, Salisbury, CT 06068
  • /23

    $2,400 per month

    • 2 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • House for Rent

    11 Raymond Ave, Canaan, CT 06018

    Located down a quiet country road on the border of North Canaan and Salisbury, this meticulously maintained 2-bedroom Cape is available for annual lease. Pull into the covered carport and enter through the mudroom, complete with generous storage and a dedicated laundry area. The open kitchen offers a new dishwasher, ample space for a dining table, and features large sliding glass doors that lead

    Brierley Hannan William Pitt Sotheby's Int'l

    11 Raymond Ave, Canaan, CT 06018
  • 151 Sand Rd, Canaan, CT 06018

    $89,250 Sold Jul 31, 2025

    • Land
    • 2.10 Acres
    • $42,500 per Acre
    • 120 Days On Market

    151 Sand Rd, Canaan, CT 06018

    This flat, primarily cleared parcel is three lots that comprise a total of 2.1 acres. It's conveniently located between North Cannan, Falls Village, and Salisbury with a sweet view of Canaan Mountain in the distance. Little to no tree removal is necessary, as much of the lot was once farmland, and active, bountiful corn fields surround the property on two sides. It's just 15 minutes to Great

    David Mallison William Pitt Sotheby's Int'l

    151 Sand Rd, Canaan, CT 06018
    • /31

      Est $473,254 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,670 Sq Ft

      166 Berkshire School Rd, Sheffield, MA 01257

      166 Berkshire School Rd, Sheffield, MA 01257
  • /32

    $425,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,700 Sq Ft

    1291 Ashley Falls Rd, Sheffield, MA 01222

    Nestled in the charming village of Ashley Falls, this cozy single-level home offers a perfect blend of comfort and scenic beauty. The open floor plan includes 2 bedrooms, 1 bath, an eat-in kitchen, and a spacious living room with a wood-burning fireplace, large picture windows, and direct access to a screened porch overlooking acres of picturesque farmland. Additional features include a slab

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 728-1649

    1291 Ashley Falls Rd, Sheffield, MA 01222
  • /14

    $3,700 per month

    • 2 Beds
    • 1 Bath
    • 868 Sq Ft
    • House for Rent

    61 Preston Ln, Salisbury, CT 06068

    Twin Lakes Lakefront Annual Rental Salisbury, CT Furnished Year-Round Rental with direct frontage on Lake Washinee, the smaller and quieter of the Twin Lakes, with a wide lawn and a Dock. $3700. per month starting June 1, 2025 (not by month or season). Features include a Front Deck, Living Room, Dining Area, Kitchen, Sunroom, Mudroom, 2 Bedrooms, 1 Full Bath, Loft, and 1-bay of the Garage. Close

    Juliet Moore Elyse Harney Real Estate

    61 Preston Ln, Salisbury, CT 06068
  • /56

    $850,000 Sold Jul 18, 2025

    • 2,430 Sq Ft
    • $350/SF
    • 53 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1979

    812 Canaan Southfield Rd, Southfield, MA 01259

    Spacious, updated and meticulously maintained modernist 4 BR/3 bath escape sits on 4.8 wooded acres, surrounded by mature birch trees and rhododendrons, seasonal creek, and a footbridge to bonus cabin in the woods. Open kitchen (Viking, Bosch)/LR layout featuring a Wittus Shaker wood stove opens to 3-sided raised deck and large screened porch. Two primary bedrooms feature sliding doors to

    Lori Rose STONE HOUSE PROPERTIES, LLC

    812 Canaan Southfield Rd, Southfield, MA 01259
  • /40

    $499,000

    • 6 Beds
    • 2.5 Baths
    • 3,184 Sq Ft

    119 S Main St, Sheffield, MA 01257

    A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 481-1637

    119 S Main St, Sheffield, MA 01257
  • /15

    $7,000 per month

    • 6 Beds
    • 3 Baths
    • 3,144 Sq Ft
    • House for Rent

    264 Twin Lakes Rd, Salisbury, CT 06068

    Available: May 26, 2025 through September 30, 2025 - Twin Lakes Lodge - Twin Lakes Lodge is a Landmark building located next to O'Hara's Marina. Features of this rental include a primary suite on the first and second floor, living room with a wood burning fireplace and a recently renovated kitchen. Enjoy entertaining or relaxing on the wrap around porch there is also a boat slip available to use

    KATHLEEN DEVANEY Elyse Harney Real Estate

    264 Twin Lakes Rd, Salisbury, CT 06068
  • /31

    $390,000 Sold Jul 15, 2025

    • 2,008 Sq Ft
    • $194/SF
    • 19 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1804

    95 Main St, Sheffield, MA 01257

    Beautiful Colonial right in the Village Center with acircular driveway and ample parking. Enter to an open kitchen and dining area with exposed beams, gracious living room with walls of windows and a family room with bar, custom stone flooring and fireplace. Convenient access from the family room to the back patio for grilling and entertaining with an exterior fireplace! The 2nd level features

    Cortney Dupont COHEN & WHITE ASSOCIATES

    95 Main St, Sheffield, MA 01257
    • /43

      Est $490,508 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,202 Sq Ft

      728 Hewins St, Sheffield, MA 01257

      728 Hewins St, Sheffield, MA 01257
  • /53

    $695,000

    • 4 Beds
    • 4 Baths
    • 3,455 Sq Ft

    64 Hewins St, Sheffield, MA 01257

    A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 296-3500

    64 Hewins St, Sheffield, MA 01257
  • /17

    $40,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • House for Rent

    23 Ravine Ridge Rd, Salisbury, CT 06068

    Secluded Salisbury Rental With Private Pool & Riverside Charm - Escape to this tranquil 3-bedroom, 2.5-bath cottage nestled at the end of a private road in Salisbury, CT. Thoughtfully furnished and brimming with charm, this home features three fireplaces, rustic brick flooring, and a three-season sunroom perfect for unwinding. Step outside to a riverside patio, where you can sip your morning

    Elyse Morris Elyse Harney Real Estate

    23 Ravine Ridge Rd, Salisbury, CT 06068
  • /40

    $1,250,000 Sold Jul 11, 2025

    • 2,100 Sq Ft
    • $595/SF
    • 12 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1984

    40 Veeley Rd, Sheffield, MA 01257

    A unique example of repurposing executed to perfection. This wonderful Gambrel style home sits on three private acres and used a lot natures offerings to help bring this home to its present glory. The home was built using the beams from a 200 year old barn that once sat on the property. The floors were milled from cherry trees that grew on the parcel, the fireplace stone is from the foundation

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    40 Veeley Rd, Sheffield, MA 01257
    • /22

      Est $656,413 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft

      169 Ashley Falls Rd, Sheffield, MA 01257

      169 Ashley Falls Rd, Sheffield, MA 01257
  • /27

    $365,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,733 Sq Ft

    101I Sand Rd, Canaan, CT 06018

    Located in a residential neighborhood on the outskirts of town, this spacious one-level home offers comfortable living with thoughtful updates throughout. The inviting floor plan features hardwood floors, a large living room, formal dining area, and a dedicated office space-perfect for working from home. The remodeled kitchen shines with custom cherry cabinets and ample counter space, ideal for

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 846-4494

    101I Sand Rd, Canaan, CT 06018
  • /35

    $75,000 per month

    • 6 Beds
    • 10 Baths
    • 9,193 Sq Ft
    • House for Rent

    325 Canaan Rd, Salisbury, CT 06068

    Luxurious Estate With Breathtaking Views In Salisbury, Ct - (Availability: $75,000/term: July 2 - September 2, 2025. $40,000/month: July or August to September 1, 2025) Escape to luxury in Salisbury, CT, with this stunning 9,000 sq. ft. estate atop a hill, offering panoramic views of the Housatonic River Valley and the Taconic Mountain Range. This 6-bedroom, 7-full-bath, and 3-half-bath home

    Elyse Morris Elyse Harney Real Estate

    325 Canaan Rd, Salisbury, CT 06068
  • 54 Rocky Ln, Salisbury, CT 06068

    $1,300,000 Sold Jun 30, 2025

    • 3,504 Sq Ft
    • $371/SF
    • 22 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 2003

    54 Rocky Ln, Salisbury, CT 06068

    This wonderful Twin lakes retreat is the perfect home for entertaining friends and relatives at all times of year. A short walk across the street leads you to the lovely, deeded lakefront access on Lake Washining, the larger of the two lakes. The home is located off a quiet, private road and set on 1.32 acres. The living room with its vaulted ceiling and wood burning fireplace greats you as you

    David Mallison William Pitt Sotheby's Int'l

    54 Rocky Ln, Salisbury, CT 06068
    • /13

      Est $464,323 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,330 Sq Ft

      1605 Clayton Mill River Rd, Southfield, MA 01259

      1605 Clayton Mill River Rd, Southfield, MA 01259
  • /10

    $345,000

    • Land
    • 37 Acres
    • $9,215 per Acre

    0 Old Turnpike Rd N, Canaan, CT 06018

    37.437 acres bordering the Konkapot River. A small portion of this land on the back side is in Massachusetts. New survey is complete. Nice location with great possibilities!

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 609-6471

    0 Old Turnpike Rd N, Canaan, CT 06018
  • /15

    $13,000 per month

    • 4 Beds
    • 3 Baths
    • 2,167 Sq Ft
    • House for Rent

    Unlisted Address

    Charming Twin Lakes Lakefront Retreat Nestled along the serene shores of Washining Lake, this beautiful 4 bedroom, 3 bath home offers a tranquil retreat for those seeking relaxation and natural beauty. With its spacious interior and breathtaking views, this rental property promises an unforgettable experience. This lake home is the perfect place to create lasting memories. Whether you seek a

    TAMI REID Northwest CT Realty

    Unlisted Address
  • /59

    $2,295,000 Sold Jun 27, 2025

    • 3,150 Sq Ft
    • $729/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1915

    246 County Rd, Sheffield, MA 01257

    Welcome to Brookland, an enchanting property of 23 acres surrounded by the Ironwork Brook. A truly move in ready home, this modern family compound has been gut renovated to the highest standards using custom Danby marble, handmade brass Italian lighting and custom cabinetry. The main house with three bedrooms and two and a half baths has oak flooring throughout, patio access from the main living

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    246 County Rd, Sheffield, MA 01257
    • /48

      Est $1,592,004 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,800 Sq Ft

      452 Shunpike Rd, Sheffield, MA 01257

      452 Shunpike Rd, Sheffield, MA 01257
  • /22

    $285,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    339 Alum Hill Rd, Sheffield, MA 01257

    Opportunity awaits the next owners of this privately situated 3 bedroom, 1.5 bath raised ranch. The first floor offers an easy layout of kitchen, laundry room, living room and three bedrooms, one with a private half bath and shared hall full bath. The lower level offers additional unfinished space for expansion and/or storage. The house is ready for updating and will make a great first, second,

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 600-0094

    339 Alum Hill Rd, Sheffield, MA 01257
  • 0 Greene Ave Unit 24079621, Canaan, CT 06018

    $40,000 Sold Jun 23, 2025

    • Land
    • 1.06 Acres
    • $37,736 per Acre
    • 105 Days On Market

    0 Greene Ave Unit 24079621, Canaan, CT 06018

    This is a rare chance to purchase a building lot with the ability to connect to town water. Newly completed survey on this 1.06 acre lot. Located above Route 44 in Greenacres on Greene Avenue with potential access from Ryan Avenue as well. Nice hardwood trees throughout the lot. Inventory is low and this is a great opportunity to build a home of your choice!

    Wendy Eichman Raynard & Peirce Realty,LLC

    0 Greene Ave Unit 24079621, Canaan, CT 06018
    • /36

      Est $407,037 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,379 Sq Ft

      1014 Salisbury Rd, Sheffield, MA 01257

      1014 Salisbury Rd, Sheffield, MA 01257
  • /35

    $649,000 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,436 Sq Ft

    27 Tobey Hill Rd, Canaan, CT 06018

    Nestled in the foothills of the Berkshires on a quiet country road, this circa 1790 colonial, "The Tobey House," awaits its new stewards! This special property features authentic period details & is sited on a majestic 3.88 acre lot with direct access to the waterfalls at Campbells Falls. The sprawling, versatile floorplan is the perfect canvas to bring your antique Pinterest board to life! With

    Tommy Connors Redfin Corporation

    27 Tobey Hill Rd, Canaan, CT 06018
  • /34

    $795,000 Sold Jun 09, 2025

    • 2,633 Sq Ft
    • $302/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1949

    371 Berkshire School Rd, Sheffield, MA 01257

    Step into a world of elegance and comfort with this gracious home, bathed in natural light and designed for sophisticated living. Set on a sprawling three-acre lot, this property features well-designed rooms that create an inviting atmosphere for both relaxation and entertainment. At the heart of the home, the updated kitchen serves as a culinary haven. The first-floor primary en-suite bedroom

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    371 Berkshire School Rd, Sheffield, MA 01257
    • /42

      Est $492,358 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft

      505 Sheffield Plain, Sheffield, MA 01257

      505 Sheffield Plain, Sheffield, MA 01257
  • /44

    $999,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,878 Sq Ft

    1166 Rannapo Rd, Sheffield, MA 01257

    It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining

    Grace Golden EQUINE HOMES REAL ESTATE, LLC

    1166 Rannapo Rd, Sheffield, MA 01257
  • 18 Patty Ln, Canaan, CT 06018

    $233,300 Sold Jun 09, 2025

    • 696 Sq Ft
    • $335/SF
    • 151 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    18 Patty Ln, Canaan, CT 06018

    This adorable Cottage is just waiting for you to call it home! Step inside to discover a compact yet efficiently organized interior encompassing 695 square feet of living space. The house features two well appointed bedrooms and a beautifully updated bathroom. A highlight of this home is the modern kitchen, complete with stainless steel appliances, luxurious quartz countertops, and sleek,

    Derek Greene Derek Greene

    18 Patty Ln, Canaan, CT 06018
    • /56

      Est $1,147,919 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,929 Sq Ft

      49 Bow Wow Rd, Sheffield, MA 01257

      49 Bow Wow Rd, Sheffield, MA 01257
  • /9

    $379,500 Pending

    • Land
    • 6 Acres
    • $60,720 per Acre

    0 S Main St, Sheffield, MA 01257

    Mountain views with Rt 7 access. Whether you are interested in a private residence to farm, raise horses, or escape the city life or if you are looking for a business opportunity with amazing Rt 7 exposure this land is the perfect opportunity. Totaling 6.25 acres of completely usable, flat, dry land. Currently the fields are hayed and have an approximate 1 acre vineyard. The 6.25 acres is

    Grace Golden EQUINE HOMES REAL ESTATE, LLC

    0 S Main St, Sheffield, MA 01257
  • 88 Lower Rd, Canaan, CT 06018

    $279,900 Sold Jun 02, 2025

    • 2,212 Sq Ft
    • $127/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    88 Lower Rd, Canaan, CT 06018

    Welcome to 88 Lower Road, North Canaan, CT-a charming 3-bedroom, 2-bathroom home nestled in a picturesque mountain setting. Built in 1965 and thoughtfully renovated in 1992, this 2,212 sq. ft. residence sits on a generous 1.31-acre lot, offering plenty of space to enjoy the serene surroundings. The home features both electric and propane heating systems, ensuring year-round comfort. A spacious

    Sean Doran William Raveis Real Estate

    88 Lower Rd, Canaan, CT 06018
    • /36

      Est $884,932 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,991 Sq Ft

      483 Home Rd, Great Barrington, MA 01230

      483 Home Rd, Great Barrington, MA 01230

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